Triethylamine → HCID 20393417, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 8-amino-5,6-dimethoxy-2,4-dimethylquinoline (20.0 g, 86 mmole), 1-iodo-4-phthalimidopentane (38.4 g, 112 mmole) and triethylamine (11.3 g, 112 mmole) in 2-ethoxyethanol (230 ml) was heated at reflux (135° C.) for 5 hr. After cooling, the solution was diluted with 5% aqueous sodium bicarbonate (0.5 l) and then extracted with methylene chloride (2× 250 ml). The combined extracts were washed with water (2× 250 ml) and brine (100 ml) and then dried (potassium carbonate). Filtration, then evaporation of the solvents, afforded a black tar. The tar was chromatographed over silica gel (0.7 kg) with benzene. The orange-brown material eluting first from the column was crystallized from ethanol (10% solution), affording 12.7 g (33%) of the title compound as orange plates, mp 141°-144°. Further recrystallization of a small amount gave an analytical sample with mp 144.5°-146.5°; the analysis was satisfactory after drying at 110° (the analysis corresponded to a hemihydrate after drying at 78°).

Provenance & Evidence